Process for the manufacture of vat dyestuffs of the anthraquinone series



WAIJTEB, MIEG,

Patented Mt. 2e,'1929.j 1,706,933

UNITED STATES PACFEN'IT OFFICE.

- on vonwmnnn, enmit AssIeNoa TO' o-aassntm mrnsrurr oonronmron, on NEW roux, N: Y., a conroaarron or nnriawann rn'oonss non. TEE monao'ruR-Eor' var nrnsrurrs on THE au'rnnaaurnonn snmns. Y 1

No Drawing. Application filed larch 22, 1327. Serial No. 177, t74, and in Germany March 24, 71926..

It has further been found that these intermediate products can easily be converted into the corresponding diphthaloyl 'acridones of The present invention relates to a process for preparing new vat dyestuffs of the anthraquinone serieshaving the general formula: v

the general formula? o I wherein the anthraquinone nuclei may be sub stituted and to dyestuifs obtainable thereby. I have found that our new dyestuffs are obtainable by causing a-l-aminoanthraquinone-2-aldehyde to be reacted upon by an alpha-halogemanthraquinone in the presence of a suitable catalyst such'as copper or a salt thereof and an acid-binding agent suchy y anhydrous Sodium acetate, intermediate action mixtures for 1-2 hours While stirring.

b b] the The conversion of the intermediateproducts a122i zfl idfih3a i a y I mto the corresponding diphthaloylacridones b 4 may be effected either by vetting and reoxidizing by means'of air or by dissolving ac ll the intermediate products in sulfuric acid,

precipitating them'with water, and heating the acid pastes to the boiling point. It is sometimes advantageous to render theacid wherein the anthraquinone nuclei may be substituted.

wherein the anthraquinone nuclei may be substituted. Y

products by dispersing the components together w ththe catalyst and the acid-binding agent na high-boiling organic solvent, as for pastes, above-mentioned, alkaline and then to heat the alkaline pastes to the boiling point.

The following examples are intended to illustrate our invention without limiting it thereto, all parts being by weight.

Example 1 -10 parts of 1-aminoanthraquinone-2-aldehyde, 10 parts of l-chloro-anthraqui'none, 7 parts of anhydrous sodium acetate and 0.1 part of copper powder are heated in 100 parts of nitrobenzene to the boiling point for about 1-2 hours while stirring until the instance nitrobenzene, and heating the re- We prefer to" prepare the intermediate prolonged time the purity of the reaction product will'be impaired. From the cooled melt brownish red crystals separate, which are filtered, washed with alcohol and water and freed from copper by boiling with a-.suit-.

able solvent, asfor example, hydrochloric acid containing copper:v chloride. With alkaline hydrosulphite a reddish-brown vat is.

obtained from which cottonis dyed in dull brownish yellow-shades. 7

The yellowish brown solution of this 1ntermediate product of the probable formula:

in concentrated sulfuric acid no longer gives the colour change characteristic for dianthraquinonyl amines neither with formaldehyde nor with boric acid. When the sulfuric acid solution is poured .-into water, a reddish brown precipitate obtained, which already yields stronger dyeings than the comgguud not treated with sulfuric acid. It will advantageous', however, to boil the preci itate' for sometime with dilute caustic so a lye until the aste has assumed a clear orange shade; T e dyestufi thus prepared having probably the formula: a

dyes cotton'from the vat clear and strong reaction product having probably the formula:

dissolves in concentrated sulfuric acid with a ellow colouration.

n order'to convert this intermediate product into the corresponding diphthaloyl acri done of 'the formula: A

t i it will be sufficient to precipitateit from its solution in concentrated sulfuric acid .by means of water-and to heat the acid paste to the boiling point. The dyestufi thus obtained dyes cotton from the vat clear brownish-yellow shades.

When' 1-benzoylamino-4-chloroanthraquinone isemployed, instead of the 5-chloro derivative, a d estufi is obtained, which dyes cotton fast dlirk" blue violet shades.

I claim z 1. In the process of preparing vat dyestuffs of the anthraquinone series the step which comprises causin'g'a l-aminoanthraquinone-2-aldehyde compound to be reacted upon by an alpha-halogenanthraquinone compound in the presence of a catalyst and an acid-binding agent.

2. In the process of preparing vat dyestuffs of the .a'nthra uinone series the step. which comgrises causing a l-aminoantliraquinone-Q- alde yde compound to be reacted upon by an 'alphwhalogenanthraquinone compound in the presence of a catalyst and an'acid-binding agent in boiling nitrobenzene.

3. In the process of preparing vat dyestufi's of the anthraquinone series the step which comprises causing a I-aminoanthraquinone-Q-aldehyde compound to be reacted upon by an alpha-chloroanthraquinone compound in the presence of copper powder and an acid-binding agent in a high-boiling 'organic diluent at elevated temperature.

4; In the process of preparing vat dyestuffs of the anthraquinone series the step which comprises causing a l-aminoanthraquinone-Z-aldehyde compound to be reacted upon by an alpha-.chloroanthraquinone compound in the presence of copper powder and an acid-binding agent in boiling nitroben zene.-

5.111 the process of preparing vat dyestufis of the anthraquinone series the step which comprises causing a l-aminoanthraquinone-2-aldehyde compound to be reacted upon by l-benzoyl-ainido-fi-chloroanthraqu-inone in the presence of catalyst and an acid-binding agent in a high-boiling organic solvent at elevated temperature. 1 6. In the process of preparing vat dyestufis of the anthraquinone series the step which, comprises causing l-aminoanthraquinone-Q-aldehyde to be reacted upon by 1- benz'oylamido-5-chloroanthraquinone in the presence of copper powder and an acid-bindmg agent in boiling nitrobenzene.

7. The process vfor the manufacture of vat dyestuffs of the .anthraquinone series which consists in causing 1-aminoanthraquinone-2- aldehyde to be reacted upon by an alpha.- chloroanthraquinone compound in the presence of a catalyst and an acid-binding agent in a high-boilin organic solvent at elevated temperature, iso ating the intermediate, roduct, dissolvmg it in concentrated su furioacid, precipitating it again by means of'water and heating the acid paste to the bOlllIlg point. v

8. The process for the manufacture of vat dyestuffs of the anthraquinone series which consists incausing 1-aminoanthraquinone-2- aldehyde to be reacted upon by an alphachloroanthraquinone compound in the pres ence of copper powder and anacid-binding agent in boiling nitrobeniene, isolating the intermediate product, dissolving it in com centrated sulfuric acid, recipitating it again by means'of water, and eating the acid paste to the boiling point. V

' 9. The process for the manufacture of vat dyestufis of the anthraquinone series which it again by meansof water, and

aldehyde to be reacted-upon by l-benzoyh amido-5-chloroanthraquinone inthe presence of copper powder and an acid-binding agent in boiling nitr'obenzene, isolating the intermediate product, dissolving it in concentrated su furicr acid, precipitating it again by means of water, and heatlng the acid paste to the boiling point.

' 12. The new vat dyestuffs of the probable general formula:

wherein one X re resents the benzo lamino group C H .GO.N and the other represents h drogen.

13. e new dyestuif of the probable formula:

mol-oo-nn E dyeing cotton from the vatvclear brownish orange shades. a

In testimony whereof, I aflix my si nature WALTER IEG. 

